ATP 250 · 1999-02-08 · draw of 32
San Jose 1999
HardFinal
| 🇦🇺 Mark Philippoussis | d. | 🇵🇭 Cecil Mamiit | 6-3 6-2 | H2H |
Semifinals
| 🇵🇭 Cecil Mamiit | d. | 🇺🇸 Michael Chang | 3-6 6-3 6-4 | H2H |
| 🇦🇺 Mark Philippoussis | d. | 🇺🇸 Pete Sampras | W/O | H2H |
Quarterfinals
| 🇵🇭 Cecil Mamiit | d. | 🇦🇺 Mark Woodforde | 7-6(5) 4-6 6-3 | H2H |
| 🇺🇸 Michael Chang | d. | 🇳🇴 Christian Ruud | 6-1 7-5 | H2H |
| 🇦🇺 Mark Philippoussis | d. | 🇺🇸 Justin Gimelstob | 6-2 3-6 7-6(0) | H2H |
| 🇺🇸 Pete Sampras | d. | 🇩🇪 Bernd Karbacher | 7-5 6-3 | H2H |
Round of 16
| 🇵🇭 Cecil Mamiit | d. | 🇺🇸 Andre Agassi | 0-6 6-6 DEF | H2H |
| 🇦🇺 Mark Woodforde | d. | 🇵🇾 Ramon Delgado | 6-2 6-3 | H2H |
| 🇺🇸 Michael Chang | d. | 🇦🇷 Franco Squillari | 6-4 7-6(5) | H2H |
| 🇳🇴 Christian Ruud | d. | 🇺🇸 Paul Goldstein | 6-1 7-6(4) | H2H |
| 🇺🇸 Justin Gimelstob | d. | 🇺🇸 Chris Woodruff | 6-4 7-6(3) | H2H |
| 🇦🇺 Mark Philippoussis | d. | 🇳🇱 John van Lottum | 6-2 6-1 | H2H |
| 🇩🇪 Bernd Karbacher | d. | 🇨🇦 Sebastien Lareau | 6-3 6-7(5) 6-3 | H2H |
| 🇺🇸 Pete Sampras | d. | 🇦🇷 Martin Rodriguez | 7-5 6-3 | H2H |
Round of 32
| 🇺🇸 Andre Agassi | d. | 🇦🇺 Todd Woodbridge | 6-2 6-1 | H2H |
| 🇵🇭 Cecil Mamiit | d. | 🇩🇰 Kenneth Carlsen | 2-6 6-3 7-5 | H2H |
| 🇦🇺 Mark Woodforde | d. | 🇺🇸 Steve Campbell | 6-3 3-6 7-5 | H2H |
| 🇵🇾 Ramon Delgado | d. | 🇳🇿 Brett Steven | 5-7 6-4 7-5 | H2H |
| 🇺🇸 Michael Chang | d. | 🇧🇷 Fernando Meligeni | 6-3 6-2 | H2H |
| 🇦🇷 Franco Squillari | d. | 🇪🇸 Albert Portas | 6-1 3-6 6-2 | H2H |
| 🇺🇸 Paul Goldstein | d. | 🇪🇸 Carlos Costa | 4-6 6-4 6-4 | H2H |
| 🇳🇴 Christian Ruud | d. | 🇦🇷 Mariano Puerta | 6-2 4-6 6-3 | H2H |
| 🇺🇸 Justin Gimelstob | d. | 🇺🇸 Jan-Michael Gambill | 6-3 7-6(6) | H2H |
| 🇺🇸 Chris Woodruff | d. | Ronald Agenor | 2-6 6-2 6-3 | H2H |
| 🇳🇱 John van Lottum | d. | 🇺🇸 Jim Courier | 6-4 7-6(4) | H2H |
| 🇦🇺 Mark Philippoussis | d. | 🇦🇲 Sargis Sargsian | 6-7(2) 7-5 6-3 | H2H |
| 🇨🇦 Sebastien Lareau | d. | 🇦🇷 Mariano Zabaleta | 6-2 6-1 | H2H |
| 🇩🇪 Bernd Karbacher | d. | 🇦🇹 Stefan Koubek | 6-3 6-2 | H2H |
| 🇦🇷 Martin Rodriguez | d. | 🇲🇽 Alejandro Hernandez | 6-4 6-7(2) 6-3 | H2H |
| 🇺🇸 Pete Sampras | d. | 🇪🇸 Galo Blanco | 6-4 6-4 | H2H |